STUDIES IN CHARACTERISATION AND DYEING BEHAVIOUR OF SOME COMPONENTS OF INDIAN MADDER (Rubia cordifolia) ON NYLON AND POLYESTER
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1 STUDIES IN CHARACTERISATION AND DYEING BEHAVIOUR OF SOME COMPONENTS OF INDIAN MADDER (Rubia cordifolia) ON NYLON AND POLYESTER by SHIPRA KUMARI DEPARTMENT OF TEXTILE TECHNOLOGY Submitted in fidfillment of the requirements of the degree of DOCTOR OF PHILOSOPHY to the INDIAN INSTITUTE OF TECHNOLOGY, Delhi July 2001
2 CERTIFICATE This is to certify that the thesis entitled "Studies in Characterisation and Dyeing Behaviour of Some Components of Indian Madder (Rubia cordifolia) on Nylon and Polyester", being submitted by Ms. Shipra Kumari, to the Indian Institute of Technology, Delhi, for the award of the degree of Doctor of Philosophy in the Department of Textile Technology, is a record of bonafide research work carried out by her. Ms. Shipra Kumari has worked under our guidance and supervision, and fulfilled the requirements for submission of the thesis. The results contained in this thesis have not been submitted, in part or in full, to any other University or Institute for the award of any degree or diploma. (DR. DEEP GUPTA) Assistant Professor, Department of Textile Technology, I.I.T., New Delhi (DR. M. L. GULRAJANI) Professor, Department of Textile Technology I.I.T., New Delhi ( )
3 PAPP74
4 ACKNOWLEDGEMENT I render my sincere thanks to my supervisors Prof. M. L. Gulrajani and Dr. Deepti Gupta for their guidance and supervision during the course of this research. I am thankful to Prof. B. L. Deopura and Prof R. B. Chavhan, present and former Head of the Department of Textile Technology, IIT, Delhi for providing facilities necessary to carry out this work. I wish to extend my thanks to Prof. P. Bajaj, Prof. K. Sen, Dr. Ashwani Kumar Agarwal and Prof. P. K. Banerjee for their kind help and support. I am thankful to all concerned authorities of Ranchi University, Ranchi, for granting me study leave and enabling me to proceed and complete my research work at Indian Institute of Technology, Delhi. I am obliged to Mrs. Akhauri Beena Kumari, Head, Dept. of Home Science, Ranchi Women's College, Ranchi for the encouragement and support received from her. The assistance and co-operation rendered by the technical staff namely Mr. Rajendra Prasad, Mr. V. A. Passi, Mr. Shiv Charan, Mr. Prakash Chand, Mr. A. K. Bhardwaj, Mr. Jagdish Parshad, Mr. Suresh Chand and Mr. K. G. Padam needs special mention. I am also thankful to my research colleagues, Mr. V. Shirish Kumar, Mr. J. N. Chakraborty and Mr. K. Murugesh Babu, for their help. It was really a great pleasure to remain in a close association of friends like Ms. Savita Maru, Ms. Chitra Krishnan, Ms. Anu Wallecha and Mr. Alok Mishra. They let me feel the real warmth of friendship. All round support and help received from them is greatly appreciated.
5 I find all words matchless to express my feelings for my parents for their adorable, consistent and unconditional support. Their help was a precious gift without which I could have never thought of this endeavor. I cherish the understanding, faith and belief of my husband. I admire his patience to bear with all the ups and downs of life that he went through alone during the period of this research thereby sparing me when my presence was needed the most. I must praise the forbearance of my young children Ayush and Ashay who uncomplainingly put up with my absence. I also acknowledge the good wishes of my parents in- laws. I want to express my honest thanks to Late Dr. A. K. Sinha and all my relatives for taking pains to help and care for my family in my absence. I must not forget the grace of God, that gave me courage, patience to bear all odd circumstances and spirit to believe in positive aspect of life. Lastly I wish to extend my gratitude to all those who directly or indirectly have aided in the completion of this research. Shipra Kumari puvr-cta
6 ABSTRACT Madder is a historical dye and has always remained a topic of research since madder dyed fabric was first found long ago in Egyptian mummies. There are two main dye yielding species of madder i.e., Rubia tinctorurn and Rubia cordifolia, out of them later one is of Indian origin. It is reported to contain several anthraquinone derivatives differing only in their substitution pattern. Chemists have undertaken the work of isolation, purification and characterisation of these anthraquinone colourants. However the characterising data presented are most often scattered and incomplete. Conflicting results have also been reported in some cases. The present work has been undertaken with the objective of developing optimised techniques for separation of major components using chromatographic methods and to generate the characterising spectroscopic data for the purified components. Efforts have also been made to study the dyeing, light and wash fastness characteristics of pure components. Methods to characterise the coloured components of the madder extract by Thin Layer Chromatography and High Performance Liquid Chromatography have been optimised. Preparative column chromatography has been used to collect the components in large amounts that can further be scaled up for commercial production. Characterisation was done using the spectroscopic techniques, such as UV- Vis, FTIR, 11-INMR, MS and melting point' These spectroscopic data can subsequently be used for identifying the components in museum textiles and for certification and authentication of natural dyes. Three major components have been purified and characterised. They are nordamncanthal (1, 3-dihydroxy-2-formyl anthraquinone), purpurin (1, 2, 4-
7 trihydroxy anthraquinone), and munjistin (1, 3-dihydroxy-2-carboxy anthraquinone). They account for approximately 80-90% of the coluring matter of the madder extract. The sensitivity of the components to temperature and ph change have been studied and reported. Purpurin was found to decompose above 90 C. The results of kinetic studies conducted showed that diffusion of dyes on nylon is good. However, the dye uptake of munjistin on polyester was poor. The rate of dyeing increased with increase in dyeing temperature. The values of diffusion coefficient and time of half dyeing of three colourants are reported. In equilibrium studies it was observed that the sorption pattern of the colourants were quite different. It was evident that the basic structure of colourant being same, the substitution group played an important role in deciding the adsorption mechanism. Munjstin having ionic group showed Langmuir isotherm on nylon showing that adsorption of dye is through site mechanism. Purpurin and nordamncanthal are sorbed by the partition mechanism because of their hydrophobic nature. Thermodynamic parameters such as affinity, heat of dyeing and entropy have been calculated and reported. Photo-fading and light fastness of these colourants on nylon were also investigated. Effect of mordant and mordanting method on colour obtained and fading rate has been studied. The light fading behavior of these anthraquinone derivatives were greatly dependent on the type and position of substituents present. Nordamncanthal and munjistin having formyl and carboxyl group respectively showed poor light resistance. Concentration of mordant affected the colour but not the fading behaviour. Post mordanting with ferrous and copper sulphate improved light resistance and slowed down the fading rate. ( v )
8 Light and wash fastness grade of dyeings with these colourants have also been evaluated and included. The various investigations clearly show that the components of madder have the same basic chemical structure i.e. hydroxy anthraquinones, but behave differently solely because of a difference in the substitution pattern.
9 CONTENTS CERTIFICATE ACKNOWLEDGEMENT ABSTRACT CONTENTS LIST OF FIGURES LIST OF TABLES Page No. ii iv vii xii xv CHAPTER 1 INTRODUCTION AND REVIEW OF LITERATURE 1.1 INTRODUCTION OBJECTIVES REVIEW OF LITERATURE NATURAL DYES EFFORTS MADE FOR REVIVAL OF NATURAL DYES RESEARCH AND DEVELOPMENT IN NATURAL DYES TECHNO-ECONOMICS OF NATURAL DYES CLASSIFICATION OF NATURAL DYES Classification on the basis of Application Method Classification on the basis of Chemical Structure NATURAL ANTHRAQU1NONE DYES Vegetable Anthraquinones Animal Anthraquinones MADDER Cultivation and Propagation Coloured Components in Madder Root Isolation and Identification of Colouring Components of Madder Turkey Red Colour and Other Metal Complexes Mutagenesis and Carcinogenesis Dyeing and Fastness Studies of Madder Recent Revival of Madder 30 i )
10 1.2.8 APPLICATION OF CHROMATOGRAPHIC METHODS FOR SEPARATION AND CHARACTERISATION OF DYES Paper Chromatography (PC) Thin Layer Chromatography (TLC) Column Chromatography (CC) High Performance Liquid Chromatography (HPLC) Gas Liquid Chromatography (GLC) APPLICATION OF SPECTROSCOPIC TECHNIQUES IN STRUCTURE DETERMINATION Ultraviolet-Visible Spectroscopy (UV-Vis) Infrared Spectroscopy (IR) Proton Nuclear Magnetic Resonance ( IHNMR) Mass Spectroscopy (MS) INTRODUCTION TO PHYSICAL CHEMISTRY OF DYEING Diffusion and Rate of Dyeing Mechanistic Models for Dye Diffusion Dye Polymer Interactions Thermodynamics of Dye Sorption STUDIES IN DYEING WITH NATURAL DYES LIGHTFADING OF DYES LIGHTFASTNESS PROPERTIES OF NATURAL DYES CONCLUSIONS 74 CHAPTER 2 CHROMATOGRAPHIC SEPARATION AND SPECTROSCOPIC CHARACTERISATION OF MAJOR COMPONENTS OF INDIAN MADDER CORDIFOLL4) (RUBIA. 2.1 INTRODUCTION EXPERIMENTAL MATERIALS METHODS Extraction of Dye Thin Layer Chromatographic Analysis (TLC) Column Chromatographic Procedure (CC) High Performance Liquid Chromatographic Procedure (HPLC) 80
11 2.2.3 INSTRUMENTS USED HPLC Melting Point Spectroscopy RESULTS AND DISCUSSION TLC ANALYSIS COLUMN CHROMATOGRAPHY HIGH PERFORMANCE LIQUID CHROMATOGRAPHIC ANALYSIS SPECTROSCOPIC CHARACTERIZATION OF ISOLATED PURE COMPONENTS Component A Component B Component E Component G CONCLUSIONS 122 CHAPTER 3 KINETICS AND THERMODYNAMICS OF DYEING NYLON AND POLYESTER WITH NATURAL ANTHRAQUINONES 3.1. INTRODUCTION EXPERIMENTAL MATERIALS METHODS Preparation of Fibres Effect of ph Effect of Temperature Estimation of Dye in Dye Bath and on Fibre Kinetic Studies Thermodynamic Studies End Group Analysis of Nylon INSTRUMENTS USED RESULTS AND DISCUSSION DYEING STUDIES WITH PURPURIN (1, 2, 4- trihydroxy anthraquinone) 129
12 Effect of ph Effect of Temperature Kinetic Study Thermodynamic Studies DYEING STUDIES WITH NORDAMNCANTHAL (1, 3 - dihydroxy-2-formyl anthraquinone) Effect of ph Effect of Temperature Kinetic Study Thermodynamic Studies DYEING STUDIES WITH MUNIISTIN (1, 3-dihydroxy - 2- carboxy anthraquinone) Effect of ph Effect of temperature Kinetic study Thermodynamic studies CONCLUSIONS 169 CHAPTER 4 PHOTOFADING OF NATURAL ANTHRAQUINONES ON NYLON 4.1 INTRODUCTION EXPERIMENTAL MATERIALS METHODS Preparation of the Fabric Dyeing Method Method of Mordant Application Kinetics of Lightfading Lightfastness Test Washfastness Test INSTRUMENTS USED RESULTS AND DISCUSSIONS KINETICS OF FADING Lightfading Of Purpurin On Nylon 184 ( x )
13 Lightfading Of Nordainncanthal On Nylon Lightfading Of Munjistin On Nylon Lightfading Of Crude Madder On Nylon LIGHTFASTNESS WASHFASTNESS CONCLUSIONS 225 CHAPTER 5 SUMMARY AND CONCLUSIONS 227 REFERENCES 232 PUBLICATIONS BIOGRAPHY
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